First days of 2023 in the Keys

Cruising Down Florida's Lee Island and South Coasts

On December 21st, we departed Tween Waters Marina on Captiva Island and began the 43 mile cruise to Naples. There is no ICW between Fort Myers Beach and Naples, so you have to go on the “outside” into the Gulf.  Wind was 10 mph out of the east as we headed south so the ocean was flat and calm as we cruised about five miles off-shore. After entering the pass at Naples, we got our first taste of south Florida boaters. There were lots of them, they were going way too fast and some were quite rude. When a big boat passes close to you leaving a large wake behind them it can really toss you around. This is called being “waked”. Well, we got ‘waked’ going into Naples. Fortunately, nothing in the salon or galley was broken, but several things were knocked out of place.

We pulled into the Naples City Marina just after lunch looking for fuel and a pump-out. They had a pump-out station, but there was no fuel due to lingering issues from Hurricane Ian back in the fall. The bath and shower facilities were nice and clean, but there was no laundry due to Ian. Later that afternoon, the looper boat Tug Bussle pulled into the marina. We had met them briefly back in Demopolis, but did not get to know them while we were there.   We got to know Russ and Janet over docktails. That evening, the four of us went over to talk with Mick Anderson on Phantom. Mick had just finished his sixth time around America’s Great Loop. Russ and I picked Micks’ brain on the route from Naples to Marathon. He graciously shared his knowledge of the southwest Florida waters and we were both grateful. After meeting with Mick, we had dinner at The Dock which is next to the City Marina. They had only been open a week since suffering damage from Hurricane Ian.

On December 23rd, we rented a car and drove an hour to the Ft. Myers airport where we picked up our daughter, Emmaline. She will be cruising with us from Naples to Marathon over the next nine days. Before we had to return the car, we made sure to provision at Publix and Costco for the week. Russ and Janet also had their two sons joining them on their boat for Christmas.  That evening, once everyone was in town, the two families had docktails under the marina pavilion.  The next day, Karen and Emmaline walked to Old Naples to explore the shops and visit the local farmer’s market.  A cold weather system rolled in that day and brought rain, wind, and much lower temperatures.  We had to unpack our coats, hats, and gloves!


Christmas day was very low key as we decided not to exchange gifts or have a big meal.  It was the most laid back Christmas we’d ever had.  The weather was cold, with a high of 50 degrees and 20 mph wind. In between rain showers that afternoon we took a walk on the beach for exercise and fresh air.   There were plenty of people enjoying it despite the weather and damage from Ian.  Karen and Emmaline made Kahlua mousse for dessert which we shared that evening with Russ, Janet and their two sons on Tug Bussle.


The cold weather in Naples was accompanied by a strong wind out of the east. This wind, combined with the low tide, made for really shallow water in the anchorage just across from the City Docks. In fact, several boats that were anchored there were resting on the bottom during low tide. One in particular appeared to have taken on water and when the tide came back in it didn’t right itself and looked as if it were going to sink. We spent a couple of afternoons trying to figure out if anyone was on the boat and if it was sinking.  A sheriff’s boat and some firemen eventually went out to check on it. It turns out there was no one on the boat, but it had taken on some water. We left Naples before we heard the end to the story regarding the half sunk boat in the anchorage.


On December 26, we traveled one mile up the harbor for fuel before departing Naples. After taking on 120 gallons of diesel, we headed to the ‘outside’ (of the Gulf) for the 14 mile cruise to Marco Island.  While it’s possible to make this trip on inland waterways, the tides were not working in our favor and it would be too shallow for us during our planned passage. The weather had warmed up and the winds had settled down so traveling on the Gulf of Mexico was no problem. However, finding a slip on Marco Island was a problem.


Originally, we had only planned to stay in Marco for two nights and then travel to Everglades City. After getting the details on cruising to Everglades City from Mick Anderson in Naples, we decided not to take the boat up there. This was primarily due to the tides being against us in the shallow channel leading to the city. Instead we wanted to stay in Marco and rent a car and drive to Everglades City. The problem was that Rose Marina in Marco only had a slip for us for two nights. Since we had planned to spend two nights in Everglades City, we now needed two more nights in Marco Island. None of the other marinas had transient slips available, so we begged and nagged the staff at Rose Marina until they found a way to let us stay a couple more nights.  Whew!  It’s very stressful not to know where you’re going to be staying from night to night.  We did have the option of anchoring in the harbor across from the marina but with all the boats coming and going this was an option of ‘last resort’.


Rose Marina was an active place. Fishing boats, tour boats and party boats were coming and going all day long. This was also a home port for the Key West Express. It’s a 150 foot jet powered catamaran ferry boat. Each day, it transported up to 200 people from Marco Island to Key West in approximately 3.5 hours. It had four huge diesel engines that drove water jets similar to a Waverunner or Jet Ski. We never saw it out in open water, but it was said to travel at 30 knots the entire trip. In the afternoon, it would make the return trip.


We launched the dinghy one afternoon and cruised around the waterways surrounding Marco Island. Since the weather had warmed up, it was a nice day. However, the wind out of the north prevented us from taking the dinghy over to the beach to look for shells.


On Thursday, we rented a car and drove to Everglades City.  We drove through town and stopped by the Museum of the Everglades to learn about the history, culture, and development of the area.  It was located in a historic laundry facility and housed many artifacts and displays about building the Tamiami Trail and developing the Everglades. Our next stop was Wooten’s for an airboat tour. None of us had ever been on an airboat before. It was a lot of fun skimming around the mangroves and looking for alligators. From there, we drove back to downtown Everglades City and had lunch at the famous Rod and Gun Club. It was a neat old place with a long history of the rich and famous staying there and fishing in the area. On advice from the Museum of the Everglades, we also drove down to Chokoloskee, which is a small community on the edge of the Ten Thousand Islands and literally in the middle of nowhere.  The advice was to visit the Smallwood store, which is the main attraction in Chokoloskee. During its ‘heyday’, it was the center of everything on the island including; general store, post office, boat ramp, polling location and police station. The store is now a museum with original artifacts dating back over 100 years.


We left Marco on December 30th and headed for an anchorage in the Everglades at the mouth of the Little Shark River.  We planned to spend one night there before heading to Marathon.  This meant we would arrive at Marathon on New Year’s Eve, a day ahead of schedule.  Fortunately, the marina in Marathon had a slip for us.


The 57 mile journey from Marco to Little Shark River took seven hours. We saw and dodged more crab pots than we thought was humanly possible. Thank goodness the weather cooperated as we had flat seas and a following wind. The anchorage was on the edge of the gulf.  And being in the Everglades, it felt like you were on the edge of the wilderness.  There was  only one other boat in the anchorage so it was also very peaceful.  Once the anchor was set, we sat on the flybridge and bow and watched dolphins play around the boat.  One down side of the light winds at an anchorage in the Everglades is the bugs. Yes, the bugs at our anchorage that evening were vicious and came out in full force as soon as the sun set. Capel braved these no-see-ums in order to grill burgers while Karen and Emmaline hid in the salon with the screen door shut.  The calm weather held throughout the night and into the next day which made for a smooth ride to Marathon in the Keys.


Did I mention crab pots? We just thought there were a lot of crab pots between Marco and Little Shark River. From Little Shark River to Marathon, there were twice as many as the day before. Sometimes they were so close together that we would have to steer 200-300 yards off course just to find a way through them.   Now that we had so many experiences with these crab pots we all decided we needed to try stone crab claws to see what the big deal was about and why there were so many people fishing for them.


On New Years Eve, we completed the 43 mile cruise to Marathon in five and a half hours. We arrived at Marlin Bay Resort and Marina in mid afternoon.  We were greeted by the concierge with a bottle of champagne and three dock hands who were ready to catch our lines, which impressed us immediately.  We connected to shore power and water and settled in for our month-long stay.  In the evening we met some of the other boaters at a NYE docktail party.  Though we did not stay up until midnight to ring in the new year, we did watch our first magnificent Keys sunset.


Development along the coast as we approach Naples
The homes get bigger as we approach Naples

Incoming weather at Naples City Dock

Sometimes weather results in beautiful sunsets


Flock of green parrots visits Naples City Dock.  They are not native to the area but enjoy hanging out on the boats and trees.

Staying warm on Naples Beach on Christmas Day

Hurricane Ian damage to Naples Pier 

Following a tour boat out of Naples Bay and into the Gulf

SkunkApe of Florida

Museum of the Everglades in Everglade City with crab pot Christmas tree

Smallwood Store in Chokoloskee, FL

Inside Smallwood Store

Wooten's Airboat Tour

Alligator on the airboat tour

Trail for airboats

Trail for airboats

Small gators, big gators, and a crocodile at Wooten's

Inside the Rod and Gun Club

Inside the Rod and Gun Club

Lunch at the Rod and Gun Club

Sunset at Little Shark River looking west into the Gulf

Sunrise at Little Shark River looking east into the Everglades

Smooth waters on the Gulf of Mexico

Beautiful colors on the Gulf of Mexico

Sunset on NYE at Marlin Bay Marina in Marathon

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